30 Days, 9 Cities, 1 Question: Where Did American Prosperity Go?
What traveling across America revealed about trust and work in the age of AI
Peter Thiel recently did an interview with the Free Press about his 2020 email to Mark Zuckerberg. The title of the piece is “Capitalism isn’t Working for Young People1”. He has benefited from capitalism more than almost anyone alive. If he admits something has failed, we need to pay attention to it. It echoes something I’ve heard everywhere this year: people feel like the system isn’t working for them anymore. Housing, student debt, AI, trust in institutions - all of it is converging into a very real sense that prosperity has gone missing.
So I spent 30 days on the road to see what prosperity looks like up close. DC, Berkeley, Baltimore, New Hampshire, New York, two cities in Florida, then Prague and Kilkenny, Ireland. The same theme surfaced: people don’t feel the prosperity that’s supposedly surrounding them. They feel the physical friction.
What became clear almost immediately is that the prosperity is real, it’s just not showing up in the places people actually live. It exists in balance sheets, in stock portfolios, in data centers behind chain-link fences. But in daily life like in commutes, in childcare costs, in housing, in safety, in community, people are feeling decay. I kept running into the same contradiction: a wealthy country where everything visible seems to be slowly breaking while everything invisible keeps getting richer.
That tension shows up everywhere, even in the way people talk about politics and culture. Thiel ties the broader culture war to economics - the rise of the groyper, angry young men2, as detailed by Rod Dreher, is rooted in the economy. As Rob writes:
I asked one astute Zoomer what the Groypers actually wanted (meaning, what were their demands). He said, “They don’t have any. They just want to tear everything down.” […] The problems are mostly economic and material, in his view (and this is something echoed by other conversations). They don’t have good career prospects, they’ll probably never be able to buy a home, many are heavily indebted with student loans that they were advised by authorities to take out, and the idea that they are likely to marry and start families seems increasingly remote.
I’ve written about the economic situation facing young people before. It does seem like same cluster of things: housing costs and the American Dream, the way social media turns everyone into a comparison engine, and the tech industry’s constant threat that you’re about to be replaced by an AI robot cyborg. Demographic shifts too - Americans aged 70 and older own almost 40% of all stocks in the US and those 55 and older own over half of all homes. It’s invisible prosperity and visible decay.
If you’re making decent money but your boss keeps hinting that AI might replace your job, and you can’t afford to buy a house in the city where you work, and the train you take doesn’t run on time (or you’re in 55 minutes of traffic or the bus never shows up or you feel unsafe or without community - you get it), you’re not going to feel prosperous. You’re going to feel like you’re treading water in a system that’s slowly giving up on you.
James Madison called institutional safeguards “auxiliary precautions” - backup systems for when civic virtue failed. But auxiliary systems only work if you can see them - if they’re trusted and functional. What happens when those safeguards themselves become invisible? When wealth compounds in hidden ways, in dark data centers, in algorithmic feeds, while the visible world like housing, transit, safety, community… cracks?
Everywhere I went, people were trying to repair something - sometimes literal infrastructure, sometimes something more abstract like a sense of purpose or a reason to believe the future might accommodate them. This is what I learned.
Part 1: The United States of America
Washington DC
When I landed in DC, the first thing I saw was the National Guard by Union Station, with their tanks parked in front of marble columns, while a man in a clown costume filmed them. Power as performance, threat as theater, all filmed by the iPhone 17.
I was there for a Brookings conference on AI and work. Senator Chris Murphy opened with a warning about AI psychosis, the blurring line between real and synthetic life.
We’ve beta-tested a cognitive experiment on an entire generation without asking for permission: first social media, now AI. An unregulated behavioral test run by private companies at national scale. But there is increasing pushback - the villain in Toy Story 5 is an iPad, and I imagine that’s going to be the beginning of a cultural shift.
There are also ways to reorient this. Tim Wu has a good piece in the NYT on how we can rightsize the very concentrated tech platform-extraction model (Meta makes 10% of its revenue from ads for scams, for example), writing:
An entire generation has grown up thinking that extraction, as opposed to building, is the path to riches […] To recover the sense of optimism and opportunity that once characterized American commerce, Americans need to be confident that — even if they don’t work for a platform — they can reap what they sow.
Ann Manov captures what this extraction economy feels like in a recent piece:
The most humiliating aspect of being alive today, I suppose, is feeling like one is living through a single, unending commercial break. As the human race disintegrates into increasingly atomized particles of recluses and rejects, one can only “stay in touch” through increasingly dystopian social media feeds that consist mostly of ads, whether traditional influencer trash and/or semi-real short-form video.
It shapes how our institutions function too. Yuval Levin argues that Congress is weak because its members want it to be weak (the shutdown is perhaps a lesson in that). They’ve abandoned the actual work of legislating in favor of what he calls “performative outrage for a partisan audience.” A congressional seat now offers a platform for building personal brands through social media engagement and cable news hits.
Success gets measured in invisible metrics like followers and fundraising emails - while the visible work of governance atrophies. It’s the same inversion: institutions optimizing for performance that compounds in attention economies while the actual infrastructure of democracy decays.
Going back to the conference, everyone on my panel agreed that AI isn’t ready for mass adoption, that there has to be some way for the supposed wealth it will generate to be redistributed, especially if it takes all the jobs. But we landed on the same cautious conclusion that AI is indeed a tool. A hammer can hang a picture or break a skull. The difference is intent.
Berkeley
That framing is helpful until you examine it. We don’t market hammers as ‘skull-crusher 1000s’ but AI gets sold explicitly as a job-taker. The CEOs are going on various podcasts and demanding the energy capacity of India3 as well as likely inevitable government backstops. The difference is who is holding the tool and what they are promising to break.
By the time I got to Berkeley a few days later, I was thinking more and more about Junior Extinction, or the apparent goal of AI to replace entry level jobs. The Berkeley AI conference had all the optimism you’d expect from the Bay Area with bright people genuinely trying to solve hard problems.
I interviewed two people I respect a lot about this, and the conversation kept circling back to the same place: we have to prepare people. Reskilling isn’t enough. The problem is not just jobs, it’s what happens to purpose and meaning when work disappears. If we erase the first step of the ladder, we can’t just tell people to climb harder.
There’s solutions, of course. An interesting paper The Death of the Social Contract and the Enshittification of Jobs explores how we can establish a federal job guarantee that prevents the degradation of work and preserve ‘dignity and purpose’ during a time of immense technological change.
After our talk, someone asked me if we were all falling prey to the Luddite mindset, which is usually shorthand for “backwards technophobe,” but the actual Luddites were more interesting than that. Luddites weren’t anti-technology. They were pro-coevolution with technology. They smashed machines when those machines were used to devalue their labor without improving their lives4.
The goal is to make technology something that extends human potential rather than reducing it to nothingness - to create visible prosperity rather than just extracting it.
Baltimore
Baltimore was the next stop, three days of conversations about whether the United States has the collective will to survive the AI era. The mood was less sunny than Berkeley. People kept using the word “bubble” - not quite accusing, more like they were testing whether anyone else would say it first.
The questions became existential very quickly. Could America remain the world’s economic center if it kept isolating itself while China industrialized at hyperspeed? If military power and economic power are the same thing, are we already losing the war? If we don’t know what we are fighting for (is it really generative AI TikTok slop? or something else?) can we fight at all?
Tracy Alloway recently compared the AI industry to coffee pods, comparing China’s commodification strategy for AI to the US valuing AI like a $5,000 espresso machine while China just gives away the Nespresso pods for free. She points out that the real AI fight is power availability, not the models. Many data centers are sitting empty because they can’t get electricity.
The valuations are wild. The return profile is shaky. China is conquering the renewable age. JP Morgan pointed out in a note recently that every iPhone user would have to pay $34 a month to drive a 10% return on all the various AI investment deployed.
This is invisible prosperity in its purest form, with billions flowing into server farms and data centers that sit empty, waiting for electricity that may never come. Meanwhile, the college graduates who were told to invest in themselves are experiencing very visible decay - working service jobs with degrees they can’t use, debt-laden, watching AI threaten to eliminate even those fallback positions.
I interviewed New York Times labor reporter Noam Scheiber in Baltimore about his forthcoming book Mutiny which tracks the downward mobility of college-educated workers and their turn toward unions. These are people who did everything right - got the degree, took on the debt - but couldn’t get jobs in their fields. So they went to work for Starbucks or REI or Amazon. Now they’re unionizing at rates that would have been unthinkable a decade ago.
Noam’s book (which you should read when it comes out) and our conversation really circled the question of work and its purpose. Support for unions among college graduates sits at 70%. The professional managerial class - supposedly individualistic, supposedly above such concerns - is converging with the working class on populist economic views. Tax the rich. Regulate big business. Protect workers from being replaced by algorithms or outsourced to cheaper labor markets.
It’s the inverse of what we’re told about education and upward mobility. The college degree was supposed to be the golden ticket. It hasn’t quite worked. Now those graduates are looking for collective solutions to individual failures that were never really individual at all.
The bubble question lingered. Have we bet everything on vapor? Or are we watching the formation of a political coalition that might actually demand something different?
New Hampshire
New Hampshire surprised me. My parents got married there 30 years ago, so they came up from Kentucky to spend a day with me. Then I went to a housing conference.
The problem everyone was trying to solve felt pretty concrete - how do you build when no one wants change? The headline answer is zoning reform, but the real answer involves water systems, sewage expansion, labor shortages, financing costs, and the politics of aging.
New Hampshire is the second-oldest state in the country. The median homeowner is in their late fifties. People can’t afford to leave and people can’t afford to move in. Rising mortgage rates have created what economists call “housing lock-in” - your 3% mortgage is now a golden handcuff.
When people can’t move, neither can labor, families, or fertility. There’s a new study showing that housing costs account for about half the US fertility decline between 2000 and 2020. It’s childcare too - a new paper from Abigail Dow reports that a 10% increase in the price of childcare leads to a 5.7% decrease in the birth rate.
The affordability crisis compounds - without affordable homes, young families don’t form. Without young families, the tax base ages. Without young taxpayers, resources shrink. The system eats itself.
In New Hampshire, people talked openly about trade-offs. They don’t have an income tax, so it relies on property taxes, already among the highest in the country, to fund services. Expanding infrastructure means higher costs somewhere. Hard problems require hard math. But there was this question underneath all of it: how do we grow without losing what feels like home?
New York City
New York felt like the opposite of that question. Not “how do we preserve what we have?” but “how do we get to yes?”
I was there for a week or so, which was the longest stop on the trip. Filmed a documentary, shot a commercial, spoke at the Aspen Ideas Conference, joined a NPR debate that felt like being in the eye of a cultural storm (read about that here). New York is exhausting and alive in equal measure. I think the present moment requires some fight with conviction in values, strength in uncertainty and New York has that in abundance.
I spoke with Dean Fuleihan a few days ago, who’s about to be first deputy mayor under Mayor-elect Zohran Mamdani (Semafor has a good write-up on Lina Khan’s role on the transition team). Mamdani’s campaign was built on affordability5, on the premise that government can work if people who believe in it actually try. Fuleihan said “New York is not about saying no. It’s about figuring out how to get to yes.”
I won’t overromanticize the city, but New York remembers itself. Maybe that’s because it’s older, or because the architecture forces you to look up. History lives in the buildings here. Being surrounded by old things makes you aware of the responsibility of keeping them standing. This is what visible investment looks like - infrastructure you can see working (at least somewhat) and architecture that reminds you something was built to last. The question is whether the will to maintain exists elsewhere.
Florida
Florida felt strange after New York. I drove from Fort Lauderdale to Marco Island to West Palm Beach, and the whole state felt like it was aging and aspiring at the same time. Lovely place.
I spoke at Palm Beach Atlantic, where my first economics professor is now Dean of the business school (he was the person who first told me that economics was an actual major - I owe him a lot!). The students were amazing. Their questions were practical: How do we afford housing? How do we navigate AI? How do we find meaning in work that might not exist in ten years?
They’re right to worry. Florida is what America could look like demographically within a decade - older, hotter, more expensive, still trying to grow. It is the most rent-burdened state in the country. You can see wealth in West Palm Beach - the waterfront towers, the private clubs , $175 million dollar condos (!) - but it’s tough to see a path toward it.
Part 2: Europe
Prague
By the time I landed in Prague, I’d spent three weeks watching Americans argue about whether we could still build anything. Prague answered soundly - yes, we can still build things.
I was there to interview Morgan Housel and give a talk on what I’ve started calling the uncertainty smoothie - AI, geopolitics, demographics, fiscal chaos, all blended into one overwhelming question mark. I was haunted by jet lag the entire trip, so I walked ten miles through the city.
It was so deliberate. Trams that ran on time. Wide sidewalks. Leaf vacuums instead of leaf blowers. Each small choice accumulated into proof that someone thought about how systems should work.
You could feel the economy in public space in trams, bridges, parks, civic buildings. Economists call this “middle-income convergence.” Czechia is catching up to Western Europe in productivity and wages, but it’s still small enough that growth is visible.
Again, in the US, growth happens in spreadsheets and server farms, in data centers behind chain-link fences that hire only 800 people for a $50b investment, on social media apps, in private, gated communities. Our prosperity is increasingly invisible. The result is this strange alienation where people sense the economy is humming somewhere, but not for them.
Economies that invest in visible competence generate trust, and trust is an economic asset. When systems decay, even rising GDP feels hollow. Infrastructure is emotional architecture. When things work, people believe life can too. Maintenance generates trust. Trust compounds.
Ireland
Ireland was the perfect final stop. My grandparents immigrated from Roscommon and Sligo in the 1950s, went back once, then came back to the States for good. Going there felt important.
I went for Kilkenomics, the world’s best economics festival. Just phenomenal. I joined four panels - a podcast with David McWilliams, one on America’s economy, another on data, and a final one on algorithms.
The audience questions were remarkable. “How would Keynes feel about all of this?” “How do we measure crony capitalism?” Everyone was wrestling with the same question that followed me all month: How do you keep a system human?
Inside Kilkenny Castle, I felt the fatigue of the trip catch up with me. The fortress has changed hands through conquest and crisis for nearly a thousand years and now stands open to anyone who wants to walk its halls.
I then climbed the narrow staircase of St. Canice’s Cathedral to the old monks’ tower. It’s been standing since the sixth century, where bells once rang to call monks to prayer. Standing there, I thought about the past month. The tanks and the clown in DC. The engineers in Berkeley. The union organizers in Baltimore. The housing advocates in New Hampshire. The students in Florida. The people in New York. The quiet competence of Prague. Everyone trying to keep something upright, whether it be an economy, a community, a sense of self.
St. Canice is the patron saint of the shipwrecked - of those who have gone through great trial and somehow survived. In a way, the tower itself is the answer to the question I’d been unknowingly chasing all month.
America’s problem isn’t that we lack wealth - we have enormous wealth - it’s that we’ve made our wealth invisible while letting everything visible decay in a way. We’ve inverted the formula.
Northern Ireland’s peace process, as Robert Saldin and Robert Eisinger wrote about succeeded partly because communities deliberately shifted focus from the existential debate between nationalists and unionists to local projects where compromise was possible. It was maintenance. Working together on visible problems created space for former enemies to reconcile themselves to living as neighbors.
When I started crying in that tower, I think it was partly exhaustion. Partly standing in a place my family came from. Partly sadness for what feels so challenging at home. Partly hope that enough people are still trying to rebuild what matters. Partly because I’d spent 30 days watching people try to make prosperity visible again - to build systems you can see, touch, and trust.
Thanks for reading.
Derek Thompson did an interesting interview with Michael Batnick and Ben Carlson
Great piece here on why we focus so much on just young men
The WSJ has a good piece on the very interconnected data center financing deals being built involving “private equity” and “30 banks” and “investment grade bonds” that pose quite a bit of blowup risk
Interesting piece from Jeremiah Johnson on what it looks like to build technology without vision and from Christopher Hale on what some see as Silicon Valley’s desire to be God
There’s an interesting article from the Cut on how “Upper East Side Moms” are reacting
Wow! What a journey. Thanks for taking us along.
Of course, we need to address inequality by moving the invisible wealth into our local systems.
Maybe we can re-frame "wealth taxes" into "system builders" and "make the wealthy feel good again."
I think a hidden part of this discussion lies in how the process of accumulating and storing wealth fundamentally changes how your brain functions. Greed, or another mental health description one could better devise, should be an official mental illness and documented/treated as such. I've come from privilege and have had a front row seat for most of my life to what happens when people accumulate or are born with massive resources. Very few are immune to these effects. I've chosen many paths towards rejecting this wealth, for better and for worse.
Until we address (or force) this fundamental human nature problem, I believe we'll continue to see forces oppose disbanding and re-distributing all the invisible wealth of the world towards building real prosperity for all.